Assistant’s Guide for Work Trips

Whether you’re preparing for your first work trip or you’ve had too many to count, tips on how to navigate the closet and stare down the ever-present-yet-never-answered question, “What should I wear?” are always welcome. Even more valued for me was learning about all the expert best practices that mileage card-carrying members have acquired in the new era of travel.

Companies are continuing to “go global” we’re all more connected than ever, as that trend continues traveling for work has become more prevalent and less reserved for the select few. That means, if you haven’t already, you’ll likely head out for business at some point over the course of your career.

I’ve been lucky enough to have traveled in almost all of my positions, but I definitely had some hiccups along the way. I’ve coupled my keenest tips with general best practices to bring you the admins guide for work trips.

Comfortable and Classy for Travel Days

Traveling can be fun and when I was growing up it always seemed like the most glamorous thing one could do, to be among the clouds. One dehumanizing TSA line after another and that façade was quickly pierced. Going through recruiting screening, being scrutinized by border patrol, and assessed by airline staff is enough to send me into a tizzy. I really don’t like it. I always feel nervous, like I’m going to get caught for something I didn’t even know I did. One of the things I’ve learned is to strategically employ is business attire. I actually work for a jeans-and-t-shirt tech company – nothing more formal than a hoodie on most people – but when I travel I always dress like I’m a friend of Meghan Markle’s. 

Why? Because as enlightened and “Woke” as everyone claims to be (at least on twitter) we still live in an image-obsessed world. A world where people “who don’t look the part” get passed over for everything from a job to an upgrade. Unfortunately, we’re not at a place in our society or globally where the content of our character enjoys its full esteem. This doesn’t mean you have to be suited and booted or have a luxury handbag. However, it does mean that even on a red-eye or early bird flight you should take care with your appearance.

Comfortable Chic is all about a delicate balance, but usually very easy to pull off. Check out some options below.


Use a carry-on, unless this is an extended trip (longer than two weeks) and even then consider laundry service. Going to baggage claim can be a drag, not to mention the real risk of having your luggage lost. (If you’ve traveled at all you know this happens.) Look, you’ve been warned. I leave the decision in your hands.

While I’m not endorsed or sponsored by them in anyways; I personally use away luggage. And I love it. But there are lots of options at varied price points.

Daily Wear

So you’ve arrived and checked in to your hotel or maybe you’re going straight to the office. Don’t be afraid to freshen up in the bathroom and do a quick change if that’s the case. If you’ve been on a long haul flight, it’s likely necessary. 

Ensure that you pack enough work-appropriate attire for every day of your trip plus two extra days. Why two extra? Because a good assistant always has a plan B and C. I’ve had an extra blazer come in handy, not for me but for another assistant on the same trip. Your forethought can be a lifesaver and you never know for whom.

The How

There are two efficient ways to get your items into your smaller carry-on. The time-honored tradition of rolling and the more modern packing cubes. I’ve been rolling my clothing for years and it works well for me. However, as I mom who travels with kids, I swear by cubes. It’s a big win to add any little extra piece of organization you can fit in when traveling with children. Whatever works best for you, you can find cubes almost anywhere from Amazon to Away. 

An Evening Out

I always bring an outfit for an evening out. What you wear will depend on where you work. If you’re in entertainment it will be quite different than if you’re in tech. Find an evening look that works for your genre that says you’re fun and approachable. Make sure it’s comfortable in case you end up traveling on to more places. (This happens quite a bit. Sometimes events can go late and even change venue).

Tech Essentials

Never forget your chargers and laptop! I had a boss who was notorious for never having a charger. It’s always there at our desk whenever we’re working so we take for granted that it’s always going to be there – until it’s not. Then we’re desperately scouring the airport for an overpriced electronics store. We’re usually easy to spot, ready to get fleeced at this-is-your-only-option airport business. (I’m not bitter, I swear!) Keep your chargers handy. If you have an extra always keep it in your luggage or be sure it’s on your packing list.

Most importantly, remember to stay hydrated. Travel can drain you and dry you out. Take care of yourself and keep plenty of water with you. On the whole, work trips shouldn’t stress you (too much). They are a fun and exciting way to get to know your colleagues better and explore new places.


I’m Ebony, I’ve been an Executive Assistant in San Francisco and Los Angeles for over 10 years. I’ve had the unique opportunity of supporting the CEO of Sephora, a globally loved cosmetics brand, working for Founder & CEOs in the tech space, including Twitch (an Amazon company), and currently working on the cutting edge of cryptocurrency. I’m passionate about innovative learning and growth centered development. The A List is a labour of love to share practical wisdom and tips on the trickiest parts of #LifeInAssistantLand


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